The intent of the work proposed herein is to carry out short stereospecific and efficient total syntheses of natural prostaglandins as well as prostaglandin analogues. Certain prostaglandins have been found to be remarkably efficacious cardiovascular agents which exhibit profound effects on blood pressure, peripheral circulation, heart rate, cardiac output, and coronary flow. Although natural sources of the prostaglandins are available, and elegant total syntheses of both natural and unnatural prostaglandins have been developed, it is nevertheless clear that a considerable need still exists for the development of practical synthetic approaches to these extremely interesting systems. The syntheses we herein propose, utilize potentially practical strategies for the construction of substituted 1,4-keto-aldehyde systems which in turn are converted into their corresponding 4-hydroxy-cyclopentenone analogues. These synthetic approaches to 4-hydroxy-cyclopentenones hold promise of being both technically simple as well as highly efficient. The synthetic schemes are designed to allow a wide number of structural variations to be introduced into the basic prostaglandin skeleton, an advantage which should be of value in preparing prostaglandin analogues. We have entered into a collaborative effort with the Pharmacy Department of the University of Rochester to test synthetic prostaglandins as well as intermediates leading to these drugs.